CA2819961C - Novel fused pyridine compounds as casein kinase inhibitors - Google Patents
Novel fused pyridine compounds as casein kinase inhibitors Download PDFInfo
- Publication number
- CA2819961C CA2819961C CA2819961A CA2819961A CA2819961C CA 2819961 C CA2819961 C CA 2819961C CA 2819961 A CA2819961 A CA 2819961A CA 2819961 A CA2819961 A CA 2819961A CA 2819961 C CA2819961 C CA 2819961C
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- CA
- Canada
- Prior art keywords
- methyl
- pyrazol
- dihydro
- pyridin
- fluorophenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000003222 pyridines Chemical class 0.000 title description 3
- 108010031425 Casein Kinases Proteins 0.000 title description 2
- 102000005403 Casein Kinases Human genes 0.000 title description 2
- 229940043355 kinase inhibitor Drugs 0.000 title description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 181
- 150000003839 salts Chemical class 0.000 claims abstract description 58
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims description 70
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 18
- 208000035475 disorder Diseases 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 208000020925 Bipolar disease Diseases 0.000 claims description 9
- 208000019022 Mood disease Diseases 0.000 claims description 9
- 208000012902 Nervous system disease Diseases 0.000 claims description 8
- 208000025966 Neurological disease Diseases 0.000 claims description 8
- 230000000926 neurological effect Effects 0.000 claims description 8
- 208000020016 psychiatric disease Diseases 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 208000019116 sleep disease Diseases 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 208000020685 sleep-wake disease Diseases 0.000 claims description 5
- 208000020401 Depressive disease Diseases 0.000 claims description 4
- 230000027288 circadian rhythm Effects 0.000 claims description 4
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- XISSYJGQGSMWHO-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-7h-furo[3,4-b]pyridin-5-one Chemical compound N=1N(C)C=C(C=2C=3C(=O)OCC=3N=CC=2)C=1C1=CC=C(F)C=C1 XISSYJGQGSMWHO-UHFFFAOYSA-N 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- YKLKIDCWMLBXQV-UHFFFAOYSA-N 1-[4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]propan-1-one Chemical compound C=12CN(C(=O)CC)CC2=NC=CC=1C1=CN(C)N=C1C1=CC=C(F)C=C1 YKLKIDCWMLBXQV-UHFFFAOYSA-N 0.000 claims 1
- MPHOHULBRJTEQS-UHFFFAOYSA-N 3-[4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-5-oxo-7h-pyrrolo[3,4-b]pyridin-6-yl]propanenitrile Chemical compound N=1N(C)C=C(C=2C=3C(=O)N(CCC#N)CC=3N=CC=2)C=1C1=CC=C(F)C=C1 MPHOHULBRJTEQS-UHFFFAOYSA-N 0.000 claims 1
- BSYXDCSTPIHJLY-UHFFFAOYSA-N 3-[[4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-5-oxo-7h-pyrrolo[3,4-b]pyridin-6-yl]methyl]benzonitrile Chemical compound N=1N(C)C=C(C=2C=3C(=O)N(CC=4C=C(C=CC=4)C#N)CC=3N=CC=2)C=1C1=CC=C(F)C=C1 BSYXDCSTPIHJLY-UHFFFAOYSA-N 0.000 claims 1
- MKTSLGTZIKIVQO-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-6,7-dihydropyrrolo[3,4-b]pyridin-5-one Chemical compound N=1N(C)C=C(C=2C=3C(=O)NCC=3N=CC=2)C=1C1=CC=C(F)C=C1 MKTSLGTZIKIVQO-UHFFFAOYSA-N 0.000 claims 1
- SFGFXQRSJQFYRR-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-6-(oxolan-3-ylmethyl)-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound N=1N(C)C=C(C=2C=3C(=O)N(CC4COCC4)CC=3N=CC=2)C=1C1=CC=C(F)C=C1 SFGFXQRSJQFYRR-UHFFFAOYSA-N 0.000 claims 1
- QMYMODQJZUCBDM-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-6-(pyridin-3-ylmethyl)-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound N=1N(C)C=C(C=2C=3C(=O)N(CC=4C=NC=CC=4)CC=3N=CC=2)C=1C1=CC=C(F)C=C1 QMYMODQJZUCBDM-UHFFFAOYSA-N 0.000 claims 1
- QTZWQUWFGJPEBB-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-6-[(1-methylpyrazol-4-yl)methyl]-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound C1=NN(C)C=C1CN1C(=O)C2=C(C=3C(=NN(C)C=3)C=3C=CC(F)=CC=3)C=CN=C2C1 QTZWQUWFGJPEBB-UHFFFAOYSA-N 0.000 claims 1
- UENLCEMZMZCOPR-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-6-[(6-methylpyridin-3-yl)methyl]-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound C1=NC(C)=CC=C1CN1C(=O)C2=C(C=3C(=NN(C)C=3)C=3C=CC(F)=CC=3)C=CN=C2C1 UENLCEMZMZCOPR-UHFFFAOYSA-N 0.000 claims 1
- GNUDHCJLTHZJDF-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-6-[2-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound CC1=NOC(CCN2C(C3=C(C=4C(=NN(C)C=4)C=4C=CC(F)=CC=4)C=CN=C3C2)=O)=N1 GNUDHCJLTHZJDF-UHFFFAOYSA-N 0.000 claims 1
- NGDXEOHYWJHBTJ-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-6-methyl-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound C=12C(=O)N(C)CC2=NC=CC=1C1=CN(C)N=C1C1=CC=C(F)C=C1 NGDXEOHYWJHBTJ-UHFFFAOYSA-N 0.000 claims 1
- JJUQDGGBCBGJJU-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-n-methyl-6,7-dihydro-5h-cyclopenta[b]pyridin-7-amine Chemical compound CNC1CCC2=C1N=CC=C2C1=CN(C)N=C1C1=CC=C(F)C=C1 JJUQDGGBCBGJJU-UHFFFAOYSA-N 0.000 claims 1
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- XZZJJXTZRSYTRF-UHFFFAOYSA-N 6-(3-ethoxypropyl)-4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound C=12C(=O)N(CCCOCC)CC2=NC=CC=1C1=CN(C)N=C1C1=CC=C(F)C=C1 XZZJJXTZRSYTRF-UHFFFAOYSA-N 0.000 claims 1
- RTEXUSDFLNHBEO-UHFFFAOYSA-N 6-(cyclopropylmethyl)-4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound N=1N(C)C=C(C=2C=3C(=O)N(CC4CC4)CC=3N=CC=2)C=1C1=CC=C(F)C=C1 RTEXUSDFLNHBEO-UHFFFAOYSA-N 0.000 claims 1
- BZOIBBGFFYYFJR-UHFFFAOYSA-N 6-[(1,5-dimethylpyrazol-3-yl)methyl]-4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound CN1C(C)=CC(CN2C(C3=C(C=4C(=NN(C)C=4)C=4C=CC(F)=CC=4)C=CN=C3C2)=O)=N1 BZOIBBGFFYYFJR-UHFFFAOYSA-N 0.000 claims 1
- QOTQMRDUISRNTF-UHFFFAOYSA-N 6-[(1,5-dimethylpyrazol-4-yl)methyl]-4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound C1=NN(C)C(C)=C1CN1C(=O)C2=C(C=3C(=NN(C)C=3)C=3C=CC(F)=CC=3)C=CN=C2C1 QOTQMRDUISRNTF-UHFFFAOYSA-N 0.000 claims 1
- XDZASHKAJTZMIT-UHFFFAOYSA-N 6-cyclopentyl-4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound N=1N(C)C=C(C=2C=3C(=O)N(C4CCCC4)CC=3N=CC=2)C=1C1=CC=C(F)C=C1 XDZASHKAJTZMIT-UHFFFAOYSA-N 0.000 claims 1
- IJWJTLLIGDSXET-UHFFFAOYSA-N 6-ethyl-4-[3-(4-fluorophenyl)-1-methylpyrazol-4-yl]-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound C=12C(=O)N(CC)CC2=NC=CC=1C1=CN(C)N=C1C1=CC=C(F)C=C1 IJWJTLLIGDSXET-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4355—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
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| US201061425213P | 2010-12-20 | 2010-12-20 | |
| US61/425,213 | 2010-12-20 | ||
| PCT/IB2011/055489 WO2012085721A1 (en) | 2010-12-20 | 2011-12-06 | Novel fused pyridine compounds as casein kinase inhibitors |
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| CA2819961A1 CA2819961A1 (en) | 2012-06-28 |
| CA2819961C true CA2819961C (en) | 2015-08-18 |
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| AR (1) | AR084412A1 (enExample) |
| AU (1) | AU2011346733C1 (enExample) |
| CA (1) | CA2819961C (enExample) |
| CY (2) | CY1118772T1 (enExample) |
| DK (2) | DK3181133T3 (enExample) |
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| HU (2) | HUE032405T2 (enExample) |
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| LT (2) | LT3181133T (enExample) |
| MX (1) | MX338551B (enExample) |
| PL (2) | PL2654750T3 (enExample) |
| PT (2) | PT2654750T (enExample) |
| RS (2) | RS59098B1 (enExample) |
| SG (1) | SG190802A1 (enExample) |
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| WO (1) | WO2012085721A1 (enExample) |
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| JP5784620B2 (ja) * | 2009-10-28 | 2015-09-24 | ファイザー・インク | カゼインキナーゼ阻害剤としてのイミダゾール誘導体 |
| US9938269B2 (en) * | 2011-06-30 | 2018-04-10 | Abbvie Inc. | Inhibitor compounds of phosphodiesterase type 10A |
| CN104837844B (zh) * | 2012-12-21 | 2017-08-29 | 百时美施贵宝公司 | 作为酪蛋白激酶1 d/e抑制剂的吡唑取代的咪唑并哌嗪 |
| WO2015163446A1 (ja) * | 2014-04-25 | 2015-10-29 | 協和発酵キリン株式会社 | イミダゾール化合物の製造方法 |
| JP2017222576A (ja) * | 2014-10-31 | 2017-12-21 | 石原産業株式会社 | 有害生物防除剤 |
| CN107365315B (zh) * | 2016-05-11 | 2024-08-09 | 国药集团国瑞药业有限公司 | 一种吡唑类化合物、其晶型及其制备方法 |
| US10973820B2 (en) * | 2017-12-13 | 2021-04-13 | Facio Intellectual Property B.V. | Compounds for treatment of diseases related to DUX4 expression |
| TW202112368A (zh) | 2019-06-13 | 2021-04-01 | 荷蘭商法西歐知識產權股份有限公司 | 用於治療有關dux4表現之疾病的抑制劑組合 |
| EP4126878A4 (en) * | 2020-03-27 | 2024-07-10 | Gritscience Biopharmaceuticals Co., Ltd. | COMPOUNDS AS CASEIN KINASE INHIBITORS |
| WO2021190616A1 (en) * | 2020-03-27 | 2021-09-30 | Gritscience Biopharmaceuticals Co., Ltd. | Methods for inhibiting casein kinases |
| AR122711A1 (es) | 2020-06-25 | 2022-09-28 | Alchemedicine Inc | COMPUESTO HETEROCÍCLICO COMO INHIBIDOR DE CASEÍNA QUINASA 1d Y/O QUINASA 5 TIPO RECEPTOR DE ACTIVINA |
| CN111808102B (zh) * | 2020-08-03 | 2021-12-31 | 南通大学 | 一种3-甲氧基-6,7-二氢-5H-吡咯并[3,4-b]吡啶盐酸盐及其合成方法 |
| JP2023541463A (ja) * | 2020-09-17 | 2023-10-02 | ヤンセン ファーマシューティカ エヌ．ベー． | カゼインキナーゼ１デルタモジュレーター |
| WO2022058920A1 (en) * | 2020-09-17 | 2022-03-24 | Janssen Pharmaceutica Nv | Casein kinase 1 delta modulators |
| EP4251149A4 (en) * | 2020-11-24 | 2024-10-30 | Merck Sharp & Dohme LLC | MODIFIED ISOINDOLINONES AS GLUCOSYLCERAMIDE SYNTHASE INHIBITORS |
| CN116888126A (zh) * | 2020-12-15 | 2023-10-13 | 北京原基华毅生物科技有限公司 | 一种酪蛋白激酶抑制剂的化合物 |
| US20230053307A1 (en) * | 2021-07-19 | 2023-02-16 | Buddhist Tzu Chi Medical Foundation | Method for preventing or treating skin disorders and conditions |
| CN119487030A (zh) * | 2022-06-14 | 2025-02-18 | 北京原基华毅生物科技有限公司 | 作为酪蛋白激酶抑制剂的化合物的盐和/或晶形 |
| CN117362303A (zh) * | 2022-07-02 | 2024-01-09 | 黑龙江联顺生物科技有限公司 | 一种生物素中间体环酐的制备方法 |
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| EP0151962A3 (en) | 1984-01-25 | 1985-10-02 | Beecham Group Plc | Pyrazolopyridine derivatives |
| NZ501112A (en) * | 1997-05-22 | 2002-10-25 | G | Substituted pyrazoles as p38 kinase inhibitors |
| US6610688B2 (en) * | 1999-12-21 | 2003-08-26 | Sugen, Inc. | 4-substituted 7-aza-indolin-2-ones and their use as protein kinase inhibitors |
| HRP20150832T1 (hr) | 2005-06-22 | 2015-09-25 | Chemocentryx, Inc. | Spojevi azaindazola i postupci njihove upotrebe |
| WO2007140213A1 (en) | 2006-05-26 | 2007-12-06 | Forest Laboratories Holdings Limited | Pyridoazepine derivatives |
| EP2308866A1 (de) * | 2009-10-09 | 2011-04-13 | Bayer CropScience AG | Phenylpyri(mi)dinylpyrazole und ihre Verwendung als Fungizide |
| JP5784620B2 (ja) * | 2009-10-28 | 2015-09-24 | ファイザー・インク | カゼインキナーゼ阻害剤としてのイミダゾール誘導体 |
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